The principal objective of this program is to develop novel, more efficient synthetic approaches to the oxidized metabolites of carcinogenic hydrocarbons. The traditional methods have involved either (a) direct introduction of a functional group at the position(s) favored for substitution, or (b) laborious total synthesis of the polycyclic ring system. The former is limited to a small fraction of the total isomers, while the latter necessitates a complex multistep synthesis for each isomer of each compound. This project is designed to explore the feasibility of potentially more efficient and more general approaches based upon employment of the parent hydrocarbon as the starting compound and utilization of blocking groups, activating groups, selective hydrogenation and other techniques to direct substitution. The hydrocarbons (BaP, BA, DMBA, etc.) to be employed are chosen for their importance as carcinogens whose metabolism has been partially elucidated and as model compounds to illustrate solutions to the synthetic problems anticipated. The compounds to be synthesized, many of which are unknown, will include arene oxides, phenols, dioloxides, bisoxides and other compounds of potential importance as metabolically activated forms of the carcinogens. It is anticipated that the synthetic principles developed will prove generally applicable to other polycyclic hydrocarbons, thereby making accessible a considerably broader range of hydrocarbon metabolites than now available.